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The Fixer

Patrick Hoge | Photo: Shaughn and John | September 21, 2018

How a political newbie from the Rust Belt became the Bay Area’s go-to negotiator, a nonprofit wizard, and a rising public policy star.

Tomiquia Moss, the CEO of Hamilton Families. Her leadership has helped Hamilton secure $30 million in funding for its Heading Home Campaign, which seeks to find permanent housing for homeless families with children in San Francisco public schools.

Editor’s Note: This is one of many stories San Francisco is publishing over the next month as part of the October 2018 Legacy Issue. To read stories as they become available online, click here.

As the Bay Area’s political, nonprofit, and entrepreneurial pooh-bahs convened on a damp and overcast morning this May to toast the opening of Salesforce Tower, all eyes—and ­cameras—were trained on CEO, philanthropist, and man of the hour Marc Benioff. When Benioff took the podium, after introducing the building and urging his fellow San Franciscans—tech moguls in particular—to put their money where their mouth is to combat inequality and homelessness, he pointed to the woman who’d been seated next to him and his wife, Lynne, in the front row, right along with acting San Francisco mayor Mark Farrell. “Tomiquia Moss,” Benioff said, urging the 41-year-old head of Hamilton Families to stand, was one of the city’s “true heroes.” By the end of the event, Benioff had pledged $3 million in personal and corporate funds to Moss’s organization, an aid agency focused on homeless families, and cited her work as foundational to his new goal of raising $200 million to eliminate homelessness in San Francisco.

The prime-time shout-out might not have registered beyond the inner circle of Bay Area power players. But for anyone keeping score, the Benioff blessing was yet another in a string of high-­profile wins for Moss, who in a few short years has emerged as an almost singularly respected figure within the world of urban development and local government—for her negotiating abilities, her fundraising skills, and her all-around political savvy. Working both inside and outside government, she’s been able to forge hard-won alliances between diverse and often adversarial interests, displaying a rare blend of wonkish policy chops and charismatic leadership skills. Oakland mayor Libby Schaaf, for whom Moss served as chief of staff during Schaaf’s first two years in office, describes her as a civic Mary Poppins, practically perfect in every way. “She descends with her umbrella, fixes things, then moves on to the next family that needs her,” Schaaf says.

Long before she became an indispensable super-nanny to Bay Area nonprofits and governments, Moss had to overcome a shattering family tragedy. Born in Cleveland, she was just a toddler when her mother died of cancer. Eleven months later, her father was shot dead on a picket line outside the Cleveland steel plant where he worked. Though three security guards were arrested on murder and related charges in the killing, a judge threw the case out midway through the trial. (The judge was later stripped of office and convicted of taking bribes, including one related to the killing of a two-year-old boy by two Hells Angels.)

Moss and her three orphaned sisters were raised by their grandmother and grandfather, a train conductor, on a 125-acre farm an hour east of Cleveland. It was peaceful there, but Moss found the surrounding community isolated and lacking in diversity: She was one of just three black students in her high school class. “I yearned for an opportunity to be in bigger towns, to see the world,” she says.

Moss’s grandmother, Ella Swiney, who died in 2016, played a crucial role in her life. “She shaped my understanding of what it’s like to be a strong black woman—that it’s OK to sit in your power around that,” Moss says. “That wasn’t always clear to me when I was growing up, because I was in the minority in my community.” Swiney also instilled in Moss an abiding concern for social justice—an understanding that “even when it’s hard, you still have a collective responsibility to help each other.”

Moss attended Ohio Wesleyan University thinking she would pursue law but changed course after interning with a mentorship program in the local public school district. That led her to another internship, with the National Low Income Housing Coalition in Washington, D.C. In 2004, Moss relocated to San Francisco and took a job as a social worker with the nonprofit Tenderloin Neighborhood Development Corporation, which specializes in acquiring affordable housing units. At night she took classes at Golden Gate University, eventually earning a master’s degree in public administration. After four years with the TNDC, Moss got her big career break: She was tapped by then-mayor Gavin Newsom’s administration to set up the Community Justice Center, an experimental alternative court that opened in 2009 with the mission of offering community-service and therapeutic alternatives to jail. Moss, who had already built relationships with city officials during her time at the TNDC and as president of the public-private Tenderloin Community Benefit District, secured the post after going on a city-financed fact-finding tour of a similar center in Brooklyn.

Moss calls the Community Justice Center job one of the most difficult of her career. Initially, critics in San Francisco vehemently denounced the initiative from all angles. Community advocates charged that it criminalized poverty and homelessness; others argued that it rewarded criminal behavior by jumping defendants to the front of the line for scarce social services. Law enforcement officials were also less than enthusiastic. But Moss won over many of these critics with impressive results. In 2014, the Rand Corporation analyzed arrest data in the Justice Center’s jurisdiction and found that the program had reduced the chance of offenders being re-arrested within a year by about 10 percent. By the time the study was completed, some 30 similar courts had opened nationwide.

The program provided evidence of Moss’s deftness at maneuvering through city bureaucracies and political obstacle courses. The only non-lawyer interviewed for the position, Moss had to find a location for the court and get 16 judicial, law enforcement, and city agencies to work together toward common goals. “It speaks volumes about how Tomiquia was perceived and received by the community that she would be seen as capable of doing that role and navigating the politics,” says Don Falk, the longtime CEO of the TNDC.

Four years after taking the Justice Center job, Moss moved to the urban planning nonprofit SPUR, where she spent nearly two years as the community planning policy director. (Moss is currently the chair of SPUR’s board of directors.) She was lured back to the public sector in late 2013 by Mayor Ed Lee to be the executive director of HOPE SF, the city’s $2.6 billion initiative to reform its troubled public housing projects. In that role, Moss helped craft an affordable housing bond initiative allotting $80 million to public housing. The bond was approved in late 2015, by which time Moss had already been hired away to serve as Mayor Schaaf’s chief of staff. Despite her brief tenure at HOPE SF, Moss won admirers for her work there, including Doug Shoemaker, who co-ran HOPE SF under Newsom. “I have an extremely high opinion of Tomiquia,” Shoemaker says. “Everywhere she’s been, you find people are incredibly enthusiastic about what kind of leader she has been.” Former supervisor and homelessness czar Bevan Dufty, who also ran HOPE SF for several years, says that part of Moss’s effectiveness comes from the fact that she doesn’t take herself too seriously. He recalls a staff retreat during which Moss, in an icebreaker exercise, performed a “killer” rendition of the running man. “Everybody just fell to the floor,” Dufty says.

After winning election in 2014, Mayor Schaaf says, she met with her “kitchen cabinet” of advisers, and together they created a dream list of qualities for a chief of staff, including “gravitas, bandwidth, credibility, quickness, decisiveness, a heart for service, and behind-the-scenes leadership abilities.” A woman on the team spoke up, saying that she knew only one person who fit the bill: Tomiquia Moss. Moss reluctantly left HOPE SF and was aboard for Schaaf’s first full day in office—just in time to be hit with a tsunami of early crises, including the fire that killed 36 people in the Ghost Ship warehouse, a police department roiled by racist text messages among officers and a lurid sex scandal, the departure of three police chiefs in the course of nine days, and Oakland’s star-crossed attempt to prevent the NFL’s Raiders from moving to Las Vegas. Throughout, however, Moss was the epitome of competence, according to Schaaf. On the day that then–police chief Paul Figueroa tendered his resignation, “I cannot tell you how angry I was,” Schaaf says. “Before I even could ask for it, she had assembled the right people in a room to make what was a very difficult and time-pressured decision. She always was one step ahead.”

Moss again had to navigate treacherous political waters when she convened and ran Schaaf’s housing cabinet, a task force that, over a nine-month period, created an eight-year housing road map for the city. The task force was made up of 110 local stakeholders—among them some unlikely bedfellows, including development interests like Bill Rosetti, a major Oakland landlord, and representatives from the tenant advocacy groups Causa Justa/Just Cause, the East Bay Community Law Center, and Centro Legal de la Raza. Here, says Ethan Guy, a senior manager at Street Level Advisors, which consulted with the city on its policy regarding equitable urban development, Moss’s interpersonal skills were put to the test. He recalls an acrimonious meeting in which a developer and a tenants’ rights advocate got into a tense disagreement. Moss, unfazed, intervened and managed to de-escalate the situation, first by getting the opponents to agree to the simple notions that they both loved Oakland and that some programs were needed to address the housing crunch. “Just being able to have and manage that conversation was giant,” Guy says. “Sometimes people have a tendency to talk over each other.”

Heather Hood, the deputy director of the nonprofit housing developer Enterprise Community Partners, was impressed by Moss’s ability to wield both carrot and stick. During the negotiations, when some people—Hood wouldn’t say who—began grumbling about the task force’s process, Moss made it clear that she’d publicly hang them out to dry if they didn’t get constructive. “Tomiquia said, ‘I don’t want to hear your complaining anymore. You need to get active and offer solutions.’ And they did,” Hood says. “She gets everybody to be their best self.”

The result was a proposal for preserving 17,000 units of affordable housing and building another 17,000 over eight years. The plan received widespread support and was unanimously adopted by the city council in September 2015. It also turned Moss into a hot political commodity—a bridge builder in an area desperately in need of one—and made a fan for life out of Schaaf, who marvels at Moss’s “ability to be tough and soft at the same time, to be organized but nimble and flexible, to get systems but also get the big picture.” Schaaf remains close with Moss, who lives in downtown Oakland with her wife and their dog and continues to be indispensable to the mayor since leaving city hall, albeit in less official ways: Schaaf still texts Moss photos of shoes she’s thinking of buying before pulling the trigger.

As Moss floats down with her umbrella once again, her latest family—or rather, families—may represent her most formidable challenge yet. Since taking over as CEO of Hamilton Families in February 2017, Moss has had the task of finding permanent housing for homeless people with children in San Francisco, building on the work of Jeff Kositsky, her immediate predecessor in the job and the current San Francisco homelessness czar. Kositsky laid the groundwork for Hamilton’s Heading Home Campaign, a public-private partnership whose focus is the city’s 1,145 homeless families with students in San Francisco public schools; the initiative’s goal is to house 800 of those families by 2020. Hamilton has found housing for about 235 families since 2016, with another 121 in the process of being housed.

It fell to Moss to close the $30 million fundraising drive needed to run the Heading Home Campaign, which had a $10 million matching-grant commitment from the Benioffs. Moss and Marc Benioff had met years earlier, when she and Schaaf visited his San Francisco home to solicit financial support for Oakland’s public schools, something that Salesforce’s nonprofit arm was already providing in San Francisco. (Salesforce.org has donated $7.7 million to Oakland schools and $27 million to San Francisco schools.)

Moss did meet the goal, aided in large part by Benioff: To date, he has personally given $11.5 million to Heading Home, and Salesforce.org has donated $3.5 million. Benioff did, however, interview Moss about the Hamilton Families program, which has been forced to house most of its recipients outside San Francisco, often disrupting their support networks. Moss explained that Hamilton was working to connect families with services in their new, less expensive cities, in order to help them maintain stable housing. Benioff was convinced: When he announced his latest donation at the Salesforce Tower event, he gushed, “What we have learned with Heading Home, and through the leadership of Tomiquia and so many people who are here, is the ­formula—the winning formula, the proven formula—for addressing homelessness.”

Schaaf envisions Moss bringing that formula to more and more people in the future. “Mark my words,” she says, “Tomiquia is running Hamilton Families, but she is thinking big.” Moss doesn’t shy away from lofty ambitions. “I see us as a leader across the region, across jurisdictions—leveraging the state to engage, leveraging national partners to engage,” she says. “I see myself leading that charge.”